This invention relates to novel pyrazole sulfonylurea herbicidal compounds, agriculturally suitable compositions thereof and a method of using them to control the growth of undesired vegetation.
New compounds effective for controlling the growth of undesired vegetation are in constant demand. In the most common situation, such compounds are sought to selectively control the growth of weeds in useful crops such as cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around fuel shortage tanks, ammunition depots and industrial storage areas. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.
The "sulfonylurea" herbicides are an extremely potent class of herbicides discovered within the last few years. A multitude of structural variations exist within the class of herbicides, but they generally consist of a sulfonylurea bridge, --SO.sub.2 NHCONH--, linking two aromatic or heteroaromatic rings.
EP-A No. 95,925 which was published 12/7/83 discloses herbicidal sulfonylureas of formula ##STR1## wherein Q is, in part, ##STR2## R.sub.10 is H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, CO.sub.2 R.sub.24, SO.sub.2 NR.sub.20 R.sub.21 or SO.sub.2 R.sub.22 ;
R.sub.11 is H, C.sub.1 -C.sub.3 alkyl, F, Cl, Br, NO.sub.2, OR.sub.16, CO.sub.2 R.sub.24, S(O).sub.m R.sub.25 or SO.sub.2 NR.sub.20 R.sub.21 ; PA1 R.sub.12 is H or CH.sub.3 ; PA1 R.sub.13 and R.sub.14 are independently H, C.sub.1 -C.sub.3 alkyl, OR.sub.16, F, Cl, Br, NO.sub.2, CO.sub.2 R.sub.24, S(O).sub.m R.sub.25 or SO.sub.2 NR.sub.20 R.sub.21 ; PA1 R.sub.15 is H or CH.sub.3. PA1 B and C are independently H, halogen, NO.sub.2, C.sub.1 -C.sub.8 alkyl, arylalkyl, C.sub.1 -C.sub.8 alkoxy, haloalkyl, CO.sub.2 R, CONR.sub.1 R.sub.2, S(O).sub.n R.sub.3, SO.sub.2 NR.sub.4 R.sub.5, or optionally substituted phenyl. PA1 B is H or lower alkyl; PA1 D is H, CO.sub.2 R or COAr, halogen, NO.sub.2 or SO.sub.2 NR.sup.1 R.sup.2 ; and PA1 Ar is phenyl optionally substituted with halogen. PA1 R.sub.1 is H or CH.sub.3 ; PA1 R.sub.2 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, halogen, nitro, C.sub.1 -C.sub.3 alkoxy, SO.sub.2 NR.sub.c R.sub.d, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfinyl, C.sub.1 -C.sub.3 alkylsulfonyl, CN, CO.sub.2 R.sub.e, C.sub.1 -C.sub.3 haloalkoxy, C.sub.1 -C.sub.3 haloalkylthio, amino, C.sub.1 -C.sub.2 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino or C.sub.1 -C.sub.2 alkyl substituted with C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 haloalkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.1 -C.sub.2 haloalkylthio, CN, OH or SH; PA1 R.sub.a and R.sub.b are independently C.sub.1 -C.sub.2 alkyl; PA1 R.sub.c is H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.3 cyanoalkyl, methoxy or ethoxy; PA1 R.sub.d is H, C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.4 alkenyl; or PA1 R.sub.c and R.sub.d may be taken together as --(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --; PA1 R.sub.e is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.2 -C.sub.4 haloalkyl, C.sub.2 -C.sub.3 cyanoalkyl, C.sub.5 -C.sub.6 cycloalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl or C.sub.2 -C.sub.4 alkoxyalkyl; PA1 R' is C.sub.3 -C.sub.5 cycloalkyl; PA1 E is a single bond or CH.sub.2 ; PA1 W is O or S; PA1 n is 0 or 1; PA1 A is ##STR12## X is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino or C.sub.3 -C.sub.5 cycloalkyl; PA1 Y is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.2 -C.sub.5 alkylthioalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkynyl, azido, cyano, C.sub.2 -C.sub.5 alkylsulfinylalkyl, C.sub.2 -C.sub.5 alkylsulfonylalkyl, ##STR13## or N(OCH.sub.3)CH.sub.3 ; m is 2 or 3; PA1 L.sub.1 and L.sub.2 are independently O or S; PA1 R.sub.3 is H or C.sub.1 -C.sub.3 alkyl; PA1 R.sub.4 and R.sub.5 are independently C.sub.1 -C.sub.3 alkyl; PA1 Z is CH or N; PA1 Z.sub.1 is CH or N; PA1 Y.sub.1 is O or CH.sub.2 ; PA1 X.sub.1 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or OCF.sub.2 H; PA1 X.sub.2 is CH.sub.3, C.sub.2 H.sub.5 or CH.sub.2 CF.sub.3 ; PA1 Y.sub.2 is OCH.sub.3, OC.sub.2 H.sub.5, SCH.sub.3, SC.sub.2 H.sub.5, CH.sub.3 or CH.sub.2 CH.sub.3 ; PA1 X.sub.3 is CH.sub.3 or OCH.sub.3 ; PA1 Y.sub.3 is H or CH.sub.3 ; PA1 X.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3 or Cl; and PA1 Y.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or Cl; PA1 (a) when X is Cl, F, Br or I, then Z is CH and Y is OCH.sub.3, OC.sub.2 H.sub.5, N(OCH.sub.3)CH.sub.3, NHCH.sub.3, N(CH.sub.3).sub.2 or OCF.sub.2 H; PA1 (b) when X or Y is C.sub.1 haloalkoxy, then Z is CH; PA1 (c) X.sub.4 and Y.sub.4 are not simultaneously Cl; PA1 (d) when W is S, then R.sub.1 is H, A is A-1 and Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, C.sub.2 H.sub.5, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH(OCH.sub.3).sub.2 or 1,3-dioxolan-2-yl; PA1 (e) when the total number of carbons of X and Y is greater than four, then the number of carbons of R must be less than or equal to two. PA1 E is a single bond; and PA1 W is O. PA1 E is CH.sub.2 ; and PA1 W is O. PA1 R.sub.2 is H, C.sub.1 -C.sub.3 alkyl, halogen, C.sub.1 -C.sub.3 alkyl substituted with 1 to 3 halogen atoms selected from 1 to 3 Cl, 1 to 3 F or 1 Br, OCH.sub.3, SO.sub.2 NHCH.sub.3, SO.sub.2 N(CH.sub.3).sub.2, S(O).sub.n CH.sub.3, CO.sub.2 CH.sub.3, CO.sub.2 CH.sub.2 CH.sub.3, OCF.sub.2 H, CH.sub.2 OCH.sub.3 or CH.sub.2 CN; PA1 X is C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, Cl, F, Br, I, OCF.sub.2 H, CH.sub.2 F, CF.sub.3, OCH.sub.2 CH.sub.2 F, OCH.sub.2 CHF.sub.2, OCH.sub.2 CF.sub.3, CH.sub.2 Cl or CH.sub.2 Br; and PA1 Y is H, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, CH.sub.2 OCH.sub.3, CH.sub.2 OCH.sub.2 CH.sub.3, NHCH.sub.3, N(OCH.sub.3)CH.sub.3, N(CH.sub.3).sub.2, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, ##STR14## OCF.sub.2 H, OCF.sub.2 Br, SCF.sub.2 H, C.tbd.CH or C.tbd.CCH.sub.3 ; 4. Compounds of Preferred 3 where PA1 R is H, C.sub.1 -C.sub.3 alkyl, phenyl, CH.sub.2 CF.sub.3 or CH.sub.2 CH.dbd.CH.sub.2 ; PA1 X is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, Cl or OCF.sub.2 H; and PA1 Y is CH.sub.3, OCH.sub.3, C.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NHCH.sub.3, or CH(OCH.sub.3).sub.2 PA1 A is A-1; PA1 R.sub.2 is H, Cl, Br, OCH.sub.3 or CH.sub.3 ; and PA1 n is 0. PA1 R is H, C.sub.1 -C.sub.3 alkyl, phenyl, CH.sub.2 CF.sub.3 or CH.sub.2 CH.dbd.CH.sub.2 ; PA1 R.sub.2 is H, Cl, Br, OCH.sub.3 or CH.sub.3 ; PA1 n is 0; PA1 A is A-1; PA1 X is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, Cl or OCF.sub.2 H; and PA1 Y is CH.sub.3, OCH.sub.3, C.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NHCH.sub.3, or CH(OCH.sub.3).sub.2.
provided that when R.sub.10 is other than C.sub.1 -C.sub.3 alkyl, then R.sub.11 is H, Cl, OCH.sub.3, NO.sub.2, or CH.sub.3 ;
provided that, when either of R.sub.13 or R.sub.14 is CO.sub.2 R.sub.24, S(O).sub.m R.sub.25 or SO.sub.2 NR.sub.20 R.sub.21, then the other is H, Cl, CH.sub.3, OCH.sub.3 or NO.sub.2 ; and
EP-A-No. 87,780 which was published 9/7/83 discloses herbicidal sulfonylureas of formula ##STR3## wherein A is H, C.sub.1 -C.sub.8 alkyl or optionally substituted phenyl;
ZA 83/3850 which was published 11/28/83 discloses compounds of formula ##STR4## wherein Q is a five-membered, heterocyclic radical which is bound by way of a carbon atom and contains 2 or 3 heteroatoms and which may be optionally substituted by halogen, pseudohalogen, nitro, alkyl, hydroxyl, haloalkyl, alkoxy, alkylthio, haloalkoxy, haloalkylthio, amino, alkylamino, dialkylamino, alkylcarbonylamino, alkylcarbonyl, alkoxycarbonyl, alkoxyalkyl, alkylthiocarbonyl, carbamoyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylsulfinyl, alkylsulfonyl, alkenyloxy or alkynyloxy; and groups such as phenyl, phenoxy or phenylthio, which are unsubstituted or substituted by halogen, nitro, cyano, alkyl, alkoxy, haloalkyl, alkylcarbonyl, alkoxycarbonyl or haloalkoxy; and also benzyl unsubstituted or substituted by halogen and/or alkyl.
Japanese Patent Application Number 58-70407 (SHO No. 59-219,218, laid open 12/10/84) discloses pyrazole-5-sulfonylureas of formula ##STR5## wherein A is H, lower alkyl or phenyl;
U.S. Pat. No. 4,370,480 discloses herbicidal sulfonylureas of formula ##STR6## wherein R.sub.1 is ##STR7## R is H; C.sub.1 -C.sub.2 alkyl; C.sub.2 -C.sub.6 alkenyl; C.sub.2 -C.sub.6 alkynyl; C.sub.1 -C.sub.4 alkyl substituted with one to four substituents selected from 0-3 F, 0-3 Cl, 0-3 Br, 0-2 OCH.sub.3, 0-1 cyano, 0-1 CO.sub.2 R.sub.1 where R.sub.1 is C.sub.1 -C.sub.3 alkyl; CO.sub.2 R.sub.1, C.sub.2 -C.sub.4 alkenyl substituted with 1-3 Cl; C.sub.3 -C.sub.6 cycloalkyl; C.sub.5 -C.sub.6 cycloalkenyl; C.sub.5 -C.sub.6 cycloalkyl substituted with substituents selected from 1-3 CH.sub.3 or one of CH.sub.3 CH.sub.2, Cl, OCH.sub.3 ; C.sub.4 -C.sub.7 cycloalkylalkyl; ##STR8## where T.sub.1 is ##STR9## or a single bond; and T is O or NOR.sub.1.sup.III